Synthesis of new N/S-containing compounds by Pd-catalyzed tandem reactions

Abstract

Two methodologies to access N/S-containing compounds via palladium-catalyzed domino reactions starting from sulfanylated N-propargyl benzimidazole derivatives are described. The first one involves a cyclocarbopalladation/reduction process and leads to medium-sized N,S-heterocycles with a stereodefined exocyclic double bond. The second one is a tandem process consisting in a Suzuki − Miyaura coupling, a desulfenylative coupling, and a totally regio/stereoselective hydrothiolation of the triple bond, which enables the reincorporation of the sulfenyl moiety into the product structure.

GRAPHICAL ABSTRACT

Keywords:

• Nitrogen-sulfur heterocycles
• medium-sized rings
• palladium catalysis
• desulfanylative coupling
• hydrothiolation

Acknowledgments

We thank the MESRI for the doctoral grant for M.C., the University of Strasbourg for the postdoctoral IdEx grant for A.B.L., and the CNRS for recurrent financial support. We thank Dr. D. Garnier and E. Oliva (PACSI, No. GDS 3670) for NMR and mass analyses.